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There is nothing “fun” about fundraising. It’s a huge pain in the
cranium. I know: I am currently raising a round of financing for
AlleyNYC. All I want to do is get back to
work, write articles for you and hang out with my awesome
girlfriend and friends. Raising money is a true dog-and-pony
show, regardless of how great your business is. You have to
explain the business model to those who want to stick a
microscope up your butt. As painful as it is, I have learned
some great things in the process:

1) Patience: You want the money and you want it
yesterday. In order to make the right decision for your business,
you must be methodical in your approach. This is one of the
biggest things that will ever happen for you and your business.
Stay calm, cool, and collected. Think Paul Newman in Cool Hand
Luke. LEGIT.

2) Representation: The right representation is
crucial. This is not just a lawyer, but a consigliere who
is going to help guide you through the process. My lawyer’s name
is Evan Bienstock and he is a badass.
He makes me feel confident going into a meeting. One of
my biggest fears is seeming like an ass to someone who could
be a huge asset to my business. A good lawyer will not just
look at the risk. He/she will guide you to a palatable deal.

3) Selection: This is a HUGE one. I know you
want to take a check from anyone, but remember: You are going to
be tied to this person/group for the life of your business. It is
a marriage and you need to think in terms of a long-term
relationship. It is essential that you get along. If you take a
check from the devil, do not be surprised when your hair catches
fire.

4) Profile your investor(s): You should profile
who you want to be your investor -- not so much who the person
is, but what they look like on paper. Profile them. An
entrepreneur who sold her company for millions of dollars, a real
estate tycoon, a grocery store chain owner, etc. Target your
demographic properly and your investor will not only write you a
check, they will be the best advisors ever. To give you a
real-life example, I wanted the most awesome media company on the
planet that covers entrepreneurs as my investor. I wanted a
publication that focuses on the inner workings of business, and
the hustlers who are making it happen. I wanted my first investor
to be Entrepreneur Media. Look at me now. They are an investor
and now I get to write to all of YOU. Now, with Entrepreneur
Media, we can show the world what we are doing at AlleyNYC. And
that is AMAZING.

5) Pay Attention to the Warning Signs: If the
person/group you are trying to raise money from is being a pain
in the ass right off the bat, this is indicative of how it will
be working with them in the future. Do you want that struggle?
I am currently doing what I call the beer test. Would I
have a beer with this person? Would I want to hang out with this
person? Obviously, there is a ton more vetting that needs to
occur than this, but if he/she or the group that you are dealing
with does not pass this test, drop them like a bad habit.

6) Wish list: Put together a list of the
group/people you would love to raise money from. Top on my list
are (in no particular order): Jay-Z (@S_C_), Russell Simmons (@UncleRUSH), Elon Musk (@elonmusk), Richard Branson (@richardbranson), Arianna Huffington
(@ariannahuff), Kevin Spacey (@KevinSpacey), Oprah (@Oprah), Sheryl Sandberg (@sherylsandberg), Barry Gosin (real estate baller), Joe
Pesci (because, as George Carlin used to say, Joe Pesci gets
“stuff” done). Obviously, this exercise is a bit ridiculous.
However, I think it’s awesome that I can publicly announce my
wish list. If any of these people would like to invest, you
can reach me at jason@alleynyc.com. In all
seriousness, having a wish list will help you profile what the
perfect investor(s) will look like (see #4).

7) Mentorship: A good mentor is key, but
especially when you are raising funds. The first investor of
AlleyNYC is David Galanter, an amazing commercial real estate
attorney, active tech investor, and friend. David is responsible
for some of the largest real estate transactions in NYC. Through
his mentorship and guidance I am able to navigate the rocky
waters of deal making.

I know that you want the investment money. We ALL do. The money
is a huge part of getting your business to the next level.
However, I strongly suggest you look into who is giving it to
you. A good partnership and meaningful relationships are some of
the most important ingredients toward success. Hustle ON.